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Phase Equilibrium Behavior of the Binary Systems CO2 + Nonadecane and CO2 + Soysolv and the Ternary System CO2 + Soysolv + Quaternary Ammonium Chloride Surfactant

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Phase Equilibrium Behavior of the Binary Systems CO2 + Nonadecane and CO2 + Soysolv and the Ternary System CO2 + Soysolv + Quaternary Ammonium Chloride Surfactant J. Chem. Eng. Data 2003, 48, 1401-1406 1401 Phase Equilibrium Behavior of the Binary Systems CO2 + Nonadecane and CO2 + Soysolv and the Ternary System CO2 + Soysolv + Quaternary Ammonium Chloride Surfactant Mohamed M. Elbaccouch,† Valeriy I. Bondar,‡ Ruben G. Carbonell,* and Christine S. Grant Box 7905sChE Department, North Carolina State University, Raleigh, North Carolina 27695-7905 Liquid phase and molar volume data were measured for the binary system CO2 + soysolv at (298.15, 313.15, 323.15, 333.15, and 343.15) K and the ternary system CO2 + soysolv + quaternary ammonium chloride surfactant at (298.15, 313.15, and 333.15) K, where the composition of soysolv to the surfactant is 99:1 wt % and 80:20 wt % on a CO2-free basis. Data were collected stoichiometrically with a high- pressure Pyrex glass cell, where no sampling or chromatographic equipment is required. The accuracy of the experimental apparatus was tested with phase equilibrium measurements for the system CO2 + nonadecane at 313.15 K. A pressure-decay technique was used to calculate the mass of CO2 loaded into the equilibrium section of the apparatus, and its accuracy was verified with a blank nitrogen experiment. The generated data show that CO2 modified soysolv is an effective transport medium for the quaternary ammonium chloride surfactant. Introduction Understanding the effects of gas solubility and swollen volume on the phase behavior of a mixture is important in various thermodynamic and industrial applications. The feasibility of using CO2, modified with a food grade oil cosolvent, as an extraction medium for particular com- pounds in chemical processes is of industrial interest. CO 2 Figure 1. Didecyldimethylammonium chloride. has been receiving industrial attention due to its solvating power, which can be altered dramatically by a slight change Table 1. Soysolv Chemical Composition4 1 in temperature or pressure. In addition, CO is a benign - 2 compound structure MW/g‚mol 1 wt % solvent, inexpensive, recyclable, nontoxic, and not flam- mable.2 Quaternary ammonium chloride surfactant (BTC methyl linoleate C19H34O2 294.5 62.4 methyl oleate C19H36O2 296.5 22.5 1010-80) is being used in the regeneration of a specific methyl palmitate C H O 270.5 8.5 packed ion exchange bed in aqueous media.3 It is desirable 17 34 2 methyl linolenate C19H32O2 292.5 3.2 to be able to recycle the surfactant and reduce its waste methyl stearate C19H38O2 298.5 3.0 volume by transporting it with CO2. The surfactant and methyl palmitoleate C17H32O2 268.4 0.3 CO2 are not miscible, but the addition of soysolv as a others na na 0.1 cosolvent to CO2 can provide the necessary solubility enhancement for removing the surfactant from the slurry oil, composed of mixed fatty acid methyl esters. The after the regeneration process. In this study, solubility data chemical composition of soysolv is given in Table 1. Its ‚ -1 for the binary system CO + soysolv and the ternary system molecular weight and boiling point are 292 g mol and 2 419 K, respectively.4 Soysolv is safe, nontoxic, and biode- CO2 + soysolv + quaternary ammonium chloride surfactant were measured. gradable. It is being used as a solvent in many cleaning The quaternary ammonium chloride surfactant contains applications, such as asphalt removal, grease and oil clean 80 wt % didecyldimethylammonium chloride, 12 wt % up, adhesive removal, welding clean up, and rubber 4 ethanol, and 8 wt % water. The ethanol and water are compound cleaning. + stabilizing agents for the didecyldimethylammonium chlo- Solubility data for the system CO2 soysolv have 5 ride to prevent precipitation. The chemical structure of received very little attention, but there are phase behavior + didecyldimethylammonium chloride is given in Figure 1. data for some of the components of soysolv CO2, such as + + + The quaternary ammonium chloride surfactant has been CO2 methyl linoleate, CO2 methyl oleate, and CO2 6-8 used industrially in disinfectant, sanitizer, and fungicidal methyl palmitate. Stoldt and Brunner measured the products for hard surfaces in hospitals and public institu- solubility of several soybean oil deodorizer distillates 9 tions.4 Also, it is an effective algaecide in swimming pools (SODDs), obtained from different plants, with CO2. SODD and industrial water treatment. Soysolv is 100% soybean does not exist in nature, but the refining process of soybean oil produces SODD, which generally comprises mixtures * To whom correspondence should be addressed. Telephone: (919) 515- of fatty acid, sterols, hydrocarbons, and vitamins. The 5118. Fax: (919) 515-583. E-mail: [email protected]. composition of SODD is similar to that of soysolv in the † Current address: Florida Solar Energy Center, 1679 Clearlake Road, sense that both contain fatty acids and ester chains. Cocoa, FL 32922. E-mail: [email protected]. ‡ Current address: RTI International, 3040 Cornwallis Road, Research We built a phase equilibrium unit capable of generating Triangle Park, NC 27709. E-mail: [email protected]. quantitative solubility and molar volume data for CO2 in 10.1021/je020201d CCC: $25.00 © 2003 American Chemical Society Published on Web 10/16/2003 1402 Journal of Chemical and Engineering Data, Vol. 48, No. 6, 2003 Figure 2. Schematic diagram of the phase equilbrium ap- Figure 3. Diagram of the visual cell and the specially designed paratus: visual cell section, everything to the right of V1; metal fitting. cell section, everything to the left of V1 and below V2. The Pyrex glass visual equilibrium cell is illustrated in 1 the liquid-phase mixture. As a preliminary step, we tested Figure 3. It has a height of 10 in. with a /2 in. o.d. body, and it tapers to a 3 in. height and a 1/ in. o.d. capillary our solubility measurement capability using a system for 4 neck. The cell is attached to 1/ in. stainless steel tubing which literature data were available at similar conditions 16 through a specially designed fitting to achieve the required to those proposed for the soysolv systems. The phase metal-to-glass pressure seal. The specially designed fitting behavior of CO2 + nonadecane was selected for comparison 1 is made from two parts. The first part is a /4 in. female because it was well studied and the published data could fitting located on the capillary neck; it is not removable 10 be used to check the accuracy of our data. We found that from the cell body (Figure 3). The second part is a our solubility and molar volume data agreed with previous 1 removable fitting containing a /16 in. female fitting from 1 5 measurements. one end and a /4 in. male fitting from the other end. A /8 In summary, we report the liquid-phase and molar in. glass circular flange is placed on the top of the capillary neck to sandwich the two parts of the fitting together. The volume data for the binary systems CO2 + nonadecane at 313.15 K and CO + soysolv at (298.15, 313.15, 323.15, visual cell is reliable to pressures of at least 10 MPa. The 2 content of the cell is stirred to achieve phase equilibrium 333.15, and 343.15) K. Also, we report the liquid-phase and using a steel ball manually actuated up and down in the molar volume data of the ternary system CO + soysolv + 2 cell by a magnet. quaternary ammonium chloride surfactant at (298.15, The pressure inside the visual cell section is measured 313.15, and 333.15) K, where the composition of soysolv to using a Heise digital pressure transducer (P1) (model 901- the surfactant is 99:1 wt % and 80:20 wt % on a CO2-free B) having a maximum working pressure of 41 MPa. The basis. The Appendix summarizes the method used to digital indicator has a resolution of 0.69 kPa and a rated calculate the mass of CO2 injected into the equilibrium cell accuracy of (6.9 kPa. The pressure inside the metal cell for the stoichiometric measurements. section is measured using an Omega pressure transducer (P2) (model DP25-S-A). Heise and Omega pressure trans- Experimental Section ducers are calibrated by their manufacturers using instru- mentation and standards that are traceable to the U.S. Apparatus. The data were generated using a stoichio- National Institute of Standards and Technology (NIST). metric technique, which involves an indirect determination Visual Cell Calibration. A calibration curve is pre- of equilibrium phase compositions. The technique does not pared relating the volume of a liquid (hexadecane, MW require sampling of equilibrium phases; it utilizes mass 226.45 g‚mol-1) in the visual cell to its height. The height balances and a volumetrically calibrated cell in determining of the liquid is measured using a cathetometer (Gaertner phase compositions. The setup used in this study is Scientific Co.; model 2778-A), which allows the volumes to represented schematically in Figure 2. It consists mainly be read in the visual cell to (0.005 cm3. The average of a visual cell section and a metal cell section. Everything deviation in the calibration curve is 0.2%.A1cm3 syringe with a 12 in. needle is used to inject a known mass of located to the right of valve 1 (V1) is considered part of the hexadecane into the visual cell (Mettler Toledo Inc.; model visual cell section. Everything located to the left of V1 and below V is considered part of the metal cell section. The AB-204). The mass of the liquid injected into the visual 2 ( visual and metal sections are housed in an acrylic water cell has an accuracy of 0.1 mg. From the known mass and density of hexadecane (0.773 g‚cm-3 at 22.4 °C), the bath.
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